This invention relates to pyridinesulfonamides which are useful as agricultural chemicals.
French Pat. No. 1,468,747 discloses the following para-substituted phenylsulfonamides, useful as antidiabetic agents: ##STR1## wherein R=H, halogen, CF.sub.3 or alkyl.
Logemann et al. Chem. Ab., 53, 18052 g (1959), disclose a number of sulfonamides, including uracil derivatives and those having the formula: ##STR2## wherein R is butyl, phenyl or ##STR3## and R.sub.1 is hydrogen or methyl. When tested for hypoglycemic effect in rats (oral doses of 25 mg/100 g), the compounds in which R is butyl and phenyl were most potent.
Wojciechowski, J. Acta. Polon. Pharm. 19, p. 125-5 (1962) [Chem. Ab., 59 1633 e] describes the synthesis of N-[(2,6-dimethoxypyrimidin-4-yl)aminocarbonyl]-4-methylbenzenesulfonamide: ##STR4## Based upon similarity to a known compound, the author predicted hypoglycemic activity for the foregoing compound.
Netherlands Pat. No. 121,788, published Sept. 15, 1966, teaches the preparation of compounds of Formula (i), and their use as general or selective herbicides, ##STR5## wherein R.sub.1 and R.sub.2 may independently be alkyl of 1-4 carbon atoms; and
R.sub.3 and R.sub.4 may independently be hydrogen, chlorine or alkyl of 1-4 carbon atoms. PA1 R'=Et, Pr, Me.sub.2 CH, Bu ##STR10## in 2, 3 and 4 position. PA1 R'=alkylcarbamoyl, cyclohexylcarbamoyl, arylcarbamoyl, CSNHCH.sub.2 CH.dbd.CH.sub.2, CONHC.sub.6 H.sub.4 Cl-p, alkylthiocarbamoyl, H, COEt; PA1 R.sup.2 =H, Me; PA1 X=NH, NMe, O, S, NEt; and PA1 n=0,1. PA1 R.sub.2 is H, Cl, Br or CH.sub.3 ; PA1 R.sub.3 and R.sub.4 are independently H or CH.sub.3 ; PA1 R.sub.5 is C.sub.1 -C.sub.6 alkyl, C.sub.3 -C.sub.6 alkenyl, CH.sub.2 CH.sub.2 OCH.sub.3, CH.sub.2 CH.sub.2 OCH.sub.2 CH.sub.3, CH.sub.2 CH.sub.2 CH.sub.2 OCH.sub.3 or CH.sub.2 CH.sub.2 Cl; PA1 R.sub.6 and R.sub.7 are independently CH.sub.3 or CH.sub.3 CH.sub.2 ; PA1 W is oxygen or sulfur; PA1 X is CH.sub.3, --OCH.sub.3 or --OCH.sub.2 CH.sub.3 ; PA1 Y is H, Cl, CH.sub.3, CF.sub.3, --NHCH.sub.3, --N(CH.sub.3).sub.2 --, --CH.sub.2 OR.sub.8, --CH.sub.2 CH.sub.2 OR.sub.8, --OCH.sub.2 CF.sub.3 or VR.sub.9 ; PA1 Z is CH or N; PA1 V is oxygen or sulfur; PA1 R.sub.8 is CH.sub.3 or CH.sub.3 CH.sub.2 ; PA1 R.sub.9 is CH.sub.3, CH.sub.3 CH.sub.2 --, CH.sub.2 CO.sub.2 R.sub.8, --CH.sub.2 CH.sub.2 OR.sub.8, C(CH.sub.3)HCO.sub.2 R.sub.8 or CH.sub.2 CH.sub.2 CO.sub.2 R.sub.8 ; PA1 Y.sub.1 is H, CH.sub.3 or OCH.sub.3 ; and PA1 X.sub.1 is H, Cl, --OCH.sub.3, --OCH.sub.2 CH.sub.3 or CH.sub.3 ; PA1 (1) both X.sub.1 and Y.sub.1 are not simultaneously hydrogen; and PA1 (2) when R is ##STR15## then R.sub.3 and R.sub.4 are both H. PA1 (1) Compounds of the generic scope wherein R.sub.3 is H and W is oxygen; PA1 (2) Compounds of preferred (1) wherein R.sub.2 is hydrogen; PA1 (3) Compounds of preferred (2) wherein R.sub.1 is Cl, NO.sub.2 or CH.sub.3 ; PA1 (4) Compounds of preferred (3) wherein R.sub.1 is chlorine; PA1 (5) Compounds of the generic scope or preferred (1)-(4) wherein R is ##STR16## (6) Compounds of preferred (5) wherein R.sub.4 is hydrogen; (7) Compounds of preferred (5) wherein R.sub.1 is chlorine; PA1 (8) Compounds of preferred (5) wherein X is CH.sub.3 or --OCH.sub.3 ; and Y is CH.sub.3, --OCH.sub.3, OCH.sub.2 CH.sub.3 or --CH.sub.2 OCH.sub.3. PA1 R.sub.12 is C.sub.1 -C.sub.12 alkyl, CH.sub.2 CH.sub.2 OH, C.sub.6 H.sub.5 or H PA1 R.sub.13 is C.sub.1 -C.sub.12 alkyl, CH.sub.2 CH.sub.2 OH, C.sub.6 H.sub.5 or H PA1 or R.sub.11 R.sub.12 R.sub.13 N= ##STR34## with the proviso that R.sub.11, R.sub.12 and R.sub.13 cannot all be phenyl at the same time. The ammonium salts of substituted pyridinesulfonamides can be prepared as described in Equation 16.
Compounds of Formula (ii), and their use as antidiabetic agents, are reported in J. Drug. Res. 6, 123 (1974). ##STR6## wherein R is pyridyl.
In U.S. Ser. No. 029,821, herbicidal compounds such as N-heterocyclic-N'(arylsulfonyl)carbamimidothioates (or compounds wherein a thienyl radical is substituted for the aryl radical), such as methyl N'-(2-chlorophenylsulfonyl)-N-(4-methoxy-6-methylpyrimidin-2-yl)carbamimid othioate are taught.
U.S. Pat. No. 3,689,549 F (Sept. 5, 1972) to R. P. Williams discloses "heterocyclic sulfonamides wherein the heteroatoms are inert can be used, e.g., compounds having the furan, thiophene or pyridine nucleus," in the production of sulfonyl isocyanates from sulfonamides in a sulfolane solvent.
B. G. Boggiano, V. Petrow, O. Stephenson and A. M. Wild, in Journal of Pharmacy and Pharmacology 13, 567-574 (1961) disclose the following compounds which were tested for hypoglycemic activity. ##STR7## where ##STR8## is in 2 or 3 position.
J. Delarge in Acta Pol. Pharm. 34, 245-249 (1977) discloses N-alkylcarbamoylpyridinesulfonamides, as described in the structure below, as mild antiinflammatory agents and strong diuretics. ##STR9## R=3-, 4-, 5-, 6-Me, 2-, 4-, 6-Cl, 3-Br, 4-ET.sub.2 N, 4-Me.sub.2 CHNH, 4-(3-ClC.sub.6 H.sub.4)NH, 4-(3-CF.sub.3 C.sub.6 H.sub.4)NH
German Pat. No. 2,516,025 (Nov. 6, 1975) to J. E. Delarge, C. L. Lapiere and A. H. Georges discloses the following compounds as inflammation inhibitors and diuretics. ##STR11## R=C.sub.6 H.sub.4 R.sup.3 (R.sup.3 =Cl, CF.sub.3, Me, MeO, H, Br, F, NO.sub.2, Et, NH.sub.2), Et, iso-Pr, 4-methylfuryl, C.sub.6 H.sub.3 Cl.sub.2 -, C.sub.6 H.sub.3 (CF.sub.3)Cl;
U.S. Pat. No. 3,346,590 (Oct. 10, 1967) (to K. Dickere and E. Kuhle) discloses the following pyridinesulfonyl isothiocyanates as novel compounds. ##STR12##
The presence of undesired vegetation causes substantial damage to useful crops, especially agricultural products that satisfy man's basic food and fiber needs, such as cotton, rice, corn, wheat, soybean and the like. The current population explosion and concomitant world food and fiber shortage demand improvements in the efficiency of producing these crops. Preventing or minimizing the loss of a portion of such valuable crops by killing or inhibiting the growth of undesired vegetation is one way of improving this efficiency.
A wide variety of materials useful for killing or inhibiting (controlling) the growth of undesired vegetation is available; such materials are commonly referred to as herbicides. The need exists, however, for still more effective herbicides that destroy or control weeds without causing significant damage to useful crops.